Materials for organic electroluminescent devices

Abstract

The present invention relates to compounds which are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing said compounds.

1 .- 11 . (canceled) 
     
     
         12 . A compound of formula (1) 
       
         
           
           
               
               
           
         
         where the symbols used are as follows: 
         X is the same or different at each instance and is CR or N; 
         X 1  is CR or N; 
         Y is CR 2 , SiR 2 , BAr, C═O, O or S; 
         Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R radicals; 
         R is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR 1 ) 2 , CHO, C(═O)R 1 , CR 1 ═C(R 1 ) 2 , CN, C(═O)OR 1 , Si(R 1 ) 3 , NO 2 , P(═O)(R 1 ) 2 , OSO 2 R 1 , OR 1 , S(═O)R 1 , S(═O) 2 R 1 , SR 1 , a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R 1  radicals, where one or more nonadjacent CH 2  groups may be replaced by —R 1 C═CR 1 —, —C≡C—, Si(R 1 ) 2 , C═O, C═S, —C(═O)O—, P(═O)(R 1 ), —O—, —S—, SO or SO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 1  radicals, where two R radicals, when they are bonded to the same carbon atom or silicon atom, may be joined to one another and may form a ring, and where two R radicals, when they are bonded to adjacent carbon atoms, may be joined to one another and may form an aliphatic or heteroaliphatic ring, and where at least one R is an aromatic or heteroaromatic ring system, and where, in the case of an electron-rich heteroaromatic ring system R, the bond of the electron-rich heteroaryl group to the base skeleton is via a carbon atom; 
         R 1  is the same or different at each instance and is H, D, F, I, B(OR 2 ) 2 , CHO, C(═O)R 2 , CR 2 ═C(R 2 ) 2 , CN, C(═O)OR 2 , Si(R 2 ) 3 , NO 2 , P(═O)(R 2 ) 2 , OSO 2 R 2 , OR 2 , S(═O)R 2 , S(═O) 2 R 2 , a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R 2  radicals and where one or more CH 2  groups in the abovementioned groups may be replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , C═O, C═S, —C(═O)O—, P(═O)(R 2 ), —O—, —S—, SO or SO 2  and where one or more hydrogen atoms in the abovementioned groups may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted in each case by one or more R 2  radicals, where two or more R 1  radicals may be joined to one another and may form a ring, where, in the case of an electron-rich heteroaromatic ring system R 1 , the bond of the electron-rich heteroaryl group to R or to the base skeleton is via a carbon atom; and 
         R 2  is the same or different at each instance and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by D or F; at the same time, two or more substituents R 2  may be joined to one another and may form a ring, where, in the case of an electron-rich heteroaromatic R 2  radical, the bond to the base skeleton is via a carbon atom. 
       
     
     
         13 . The compound as claimed in  claim 12 , wherein the compound is a compound of the formulae (2) or (3) 
       
         
           
           
               
               
           
         
         where the symbols used have the definitions given in  claim 12 . 
       
     
     
         14 . The compound as claimed in  claim 12 , wherein not more than two symbols X per cycle are N. 
     
     
         15 . The compound as claimed in  claim 12 , wherein the compound is a compound of the formulae (4) and (5) 
       
         
           
           
               
               
           
         
         where the symbols used have the definitions given in  claim 12 . 
       
     
     
         16 . The compound as claimed in  claim 12 , wherein the compound is a compound of the formulae (6) to (8) 
       
         
           
           
               
               
           
         
         where the symbols used have the definitions given in  claim 12 . 
       
     
     
         17 . The compound as claimed in  claim 12 , wherein the compound is a compound of the formulae (9) to (16) 
       
         
           
           
               
               
           
         
         where the symbols used have the definitions given in  claim 12 . 
       
     
     
         18 . A process for preparing the compound as claimed in  claim 12 , which comprises the following steps:
 (A) synthesizing the base skeleton of formula (1) that still does not bear an R group representing an aromatic or heteroaromatic ring system; and   (B) introducing this R group by at least one coupling reaction.   
     
     
         19 . A formulation comprising at least one compound as claimed in  claim 12  and at least one further compound and/or at least one solvent. 
     
     
         20 . An electronic device comprising at least one compound as claimed in  claim 12 . 
     
     
         21 . An electronic device comprising the formulation as claimed in  claim 19 . 
     
     
         22 . An organic electroluminescent device comprising the compound as claimed in  claim 12  is used in an emitting layer as matrix material for phosphorescent or fluorescent emitters or for emitters that exhibit TADF (thermally activated delayed fluorescence), and/or in an electron transport layer and/or in a hole blocker layer and/or in a hole transport layer and/or in an exciton blocker layer.